US5382330A - Separation of 1-octene from octane by azeotropic distillation - Google Patents
Separation of 1-octene from octane by azeotropic distillation Download PDFInfo
- Publication number
- US5382330A US5382330A US08/209,252 US20925294A US5382330A US 5382330 A US5382330 A US 5382330A US 20925294 A US20925294 A US 20925294A US 5382330 A US5382330 A US 5382330A
- Authority
- US
- United States
- Prior art keywords
- octene
- octane
- separation
- azeotropic distillation
- forming agent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 title claims abstract description 64
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 title claims abstract description 61
- 238000010533 azeotropic distillation Methods 0.000 title abstract description 9
- 238000000926 separation method Methods 0.000 title description 9
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 15
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 8
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 claims 2
- 238000009835 boiling Methods 0.000 abstract description 3
- 238000004821 distillation Methods 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 150000002894 organic compounds Chemical class 0.000 description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000005357 flat glass Substances 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- UGVSFVJLBBWBRE-UHFFFAOYSA-N octane oct-1-ene Chemical compound CCCCCCCC.CCCCCCC=C UGVSFVJLBBWBRE-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
- C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
- C07C7/06—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by azeotropic distillation
Definitions
- This invention relates to a method for separating 1-octene from octane using certain organic liquids as the agent in azeotropic distillation.
- Azeotropic distillation is the method of separating close boiling compounds or azeotropes from each other by carrying out the distillation in a multiplate rectification column in the presence of an added liquid said liquid forming an azeotrope with one or both of the compounds to be separated. Its presence on each plate of the rectification column alters the relative volatility in a direction to make the separation on each plate greater and thus require either fewer plates to effect the same separation or make possible a greater degree of separation with the same number of plates.
- the azeotrope forming agent is introduced with the feed to a continuous column. The azeotrope forming agent and the more volatile component are taken off as overhead product and the less volatile component comes off as bottoms product.
- the usual methods of separating the azeotrope former from the more volatile component are cooling and phase separation or solvent extraction.
- Table 1 shows the relative volatility required to get 99% purity. With no agent, the relative volatility is 1.2 and 68 actual plates are required. With an agent giving a relative volatility of 1.9, only twenty plates are required.
- the object of this invention is to provide a process or method of azeotropic distillation that will enhance the relative volatility of 1-octene from octane in their separation in a rectification column. It is a further object of this invention to identify organic compounds which in addition to the above constraints, are stable, can be separated from 1-octene and recycled to the azeotrope column with little decomposition.
- the objects of this invention are provided by a process for separating 1-octene from octane which entails the use of certain organic compound as the agent in azeotropic distillation.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Abstract
1-Octene is difficult to separate from octane by conventional distillation or rectification because of the proximity of their boiling points. 1-Octene can be readily separated from octane by azeotropic distillation. Effective agents are ethyl formate, ethyl acetate and t-amyl methyl ether.
Description
This invention relates to a method for separating 1-octene from octane using certain organic liquids as the agent in azeotropic distillation.
Azeotropic distillation is the method of separating close boiling compounds or azeotropes from each other by carrying out the distillation in a multiplate rectification column in the presence of an added liquid said liquid forming an azeotrope with one or both of the compounds to be separated. Its presence on each plate of the rectification column alters the relative volatility in a direction to make the separation on each plate greater and thus require either fewer plates to effect the same separation or make possible a greater degree of separation with the same number of plates. The azeotrope forming agent is introduced with the feed to a continuous column. The azeotrope forming agent and the more volatile component are taken off as overhead product and the less volatile component comes off as bottoms product. The usual methods of separating the azeotrope former from the more volatile component are cooling and phase separation or solvent extraction.
In the Fischer-Tropsch process for converting carbon monoxide and hydrogen into liquids, gases and waxes, hundreds of different hydrocarbons and oxygenated compounds are formed, most of them in very small amounts. One valuable compound occuring in reasonable quantities is 1-octene, b.p.=123° C. When this compound is separated by precision fractionation, all but the closest boiling compounds are separated. The closest is octane, b.p.=126° C. Azeotropic distillation would be an attractive method of effecting the separation of 1-octene from octane if agents can be found that will (1) create a large apparent relative volatility between 1-octene and octane and (2) are easy to recover from 1-octene. 1-Octene and octane boil three degrees apart and thus are impractical to separate by conventional rectification. Table 1 shows the relative volatility required to get 99% purity. With no agent, the relative volatility is 1.2 and 68 actual plates are required. With an agent giving a relative volatility of 1.9, only twenty plates are required.
TABLE 1
______________________________________
Theoretical and Actual Plates Required vs.
Relative Volatility for 1-Octene - Octane Separation
Relative
Theoretical Plates Required
Actual Plates Required,
Volatility
At Total Reflux, 99% Purity
75% Efficiency
______________________________________
1.2 51 68
1.5 23 31
1.9 15 20
______________________________________
The object of this invention is to provide a process or method of azeotropic distillation that will enhance the relative volatility of 1-octene from octane in their separation in a rectification column. It is a further object of this invention to identify organic compounds which in addition to the above constraints, are stable, can be separated from 1-octene and recycled to the azeotrope column with little decomposition.
The objects of this invention are provided by a process for separating 1-octene from octane which entails the use of certain organic compound as the agent in azeotropic distillation.
I have discovered that certain organic compounds will greatly improve the relative volatility of 1-octene to octane and permit the separation of 1-decene from decane by rectification when employed as the agent in extractive distillation. They are methyl acetate, ethyl acetate, ethyl formate, t-amyl methyl ether and dimethylacetamide.
TABLE 2
______________________________________
Effective Azeotropic Distillation Agents For
separating 1-Octene From Octane
Relative
Compounds Volatility
______________________________________
None 1.2
Methyl acetate 1.5
Ethyl acetate 1.6
Ethyl formate 1.9 *
t-Amyl methyl ether
1.8 *
Dimethylacetamide
1.5
______________________________________
* Brings octane out as overhead product
The usefulness or utility of this invention can be demonstrated by referring to the data presented in Tables 1 and 2. All of the successful agents show that 1-octene can be separated from octane by means of azeotropic distillation in a rectification column and that the ease of separation as measured by relative volatility is considerable.
Twenty grams of octane, 80 grams of 1-octene and 50 grams of ethyl acetate were charged to a vapor-liquid equilibrium still and refluxed for twelve hours. Analysis indicates a vapor composition of 21.3% octane, 78.7% 1-octene; a liquid composition of 30.6% octane, 69.4% 1-octene. This is a relative volatility of 1.6.
Sixty grams of 1-octene, 40 grams of octane and 150 grams of t-amyl methyl ether were placed in the stillpot of a 7.3 theoretical plate glass perforated plate rectification column and refluxed for four hours. The overhead composition was 99.2% octane, 0.8% 1-octene; the bottoms composition was 60.7% octane, 39.3% 1-octene which is a relative volatility of 1.82.
Sixty grams of 1-octene, 40 grams of octane and 150 grams of ethyl formate were placed in the stillpot of a 7.3 theoretical plate glass perforated plate rectification and refluxed for four hours. The overhead composition was 97.9% octane, 2.1% 1-octene; the bottoms composition was 28.3% octane, 71.7% 1-octene which is a relative volatility of 1.93.
Claims (2)
1. A method for recovering 1-octene from a mixture of 1-octene and octane which comprises distilling a mixture of 1-octene and octane in the presence of an azeotrope forming agent, recovering the octane and the azeotrope forming agent as overhead product and obtaining the 1-octene as bottoms product, wherein said azeotrope forming agent consists of one material selected from the group consisting of ethyl formate and t-amyl methyl ether.
2. A method for recovering 1-octene from a mixture of 1-octene and octane which comprises distilling a mixture of 1-octene and octane in the presence of an azeotrope forming agent, recovering the 1-octene and the azeotrope forming agent as overhead product and obtaining the octane as bottoms product, wherein said azeotrope forming agent consists of one material selected from the group consisting of methyl acetate, ethyl acetate and dimethylacetamide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/209,252 US5382330A (en) | 1994-03-14 | 1994-03-14 | Separation of 1-octene from octane by azeotropic distillation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/209,252 US5382330A (en) | 1994-03-14 | 1994-03-14 | Separation of 1-octene from octane by azeotropic distillation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US5382330A true US5382330A (en) | 1995-01-17 |
Family
ID=22778013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US08/209,252 Expired - Fee Related US5382330A (en) | 1994-03-14 | 1994-03-14 | Separation of 1-octene from octane by azeotropic distillation |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US5382330A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5510006A (en) * | 1995-05-25 | 1996-04-23 | International Flavors & Fragrances Inc. | Process for separation of vanillin by means of azeotropic distillation with dibenzyl ether |
| US6590132B1 (en) | 2001-04-27 | 2003-07-08 | Uop Llc | Separation of monomer from oligomer with lower bottoms temperature |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2186524A (en) * | 1935-07-26 | 1940-01-09 | Phillips Petroleum Co | Process of increasing the concentration of olefins in a mixture containing olefins and paraffins |
| US2461993A (en) * | 1943-08-23 | 1949-02-15 | Union Oil Co | Hydrocarbon separation by azeotropic distillation |
| US3087866A (en) * | 1960-12-09 | 1963-04-30 | Union Carbide Corp | Recovery of olefins from c7 to c9 corresponding olefin-paraffin mixtures |
| US5100515A (en) * | 1990-10-26 | 1992-03-31 | Phillips Petroleum Company | Separation of alkenes from close-boiling alkanes |
-
1994
- 1994-03-14 US US08/209,252 patent/US5382330A/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2186524A (en) * | 1935-07-26 | 1940-01-09 | Phillips Petroleum Co | Process of increasing the concentration of olefins in a mixture containing olefins and paraffins |
| US2461993A (en) * | 1943-08-23 | 1949-02-15 | Union Oil Co | Hydrocarbon separation by azeotropic distillation |
| US3087866A (en) * | 1960-12-09 | 1963-04-30 | Union Carbide Corp | Recovery of olefins from c7 to c9 corresponding olefin-paraffin mixtures |
| US5100515A (en) * | 1990-10-26 | 1992-03-31 | Phillips Petroleum Company | Separation of alkenes from close-boiling alkanes |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5510006A (en) * | 1995-05-25 | 1996-04-23 | International Flavors & Fragrances Inc. | Process for separation of vanillin by means of azeotropic distillation with dibenzyl ether |
| US5772909A (en) * | 1995-05-25 | 1998-06-30 | International Flavors & Fragrances Inc. | Process for separation of vanillin from other chemicals by means of azeotropic distillation with dibenzyl ether and mixtures of vanillin and dibenzyl ether used in such process |
| US6590132B1 (en) | 2001-04-27 | 2003-07-08 | Uop Llc | Separation of monomer from oligomer with lower bottoms temperature |
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|---|---|---|---|
| REMI | Maintenance fee reminder mailed | ||
| FPAY | Fee payment |
Year of fee payment: 4 |
|
| SULP | Surcharge for late payment | ||
| LAPS | Lapse for failure to pay maintenance fees | ||
| STCH | Information on status: patent discontinuation |
Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362 |
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| FP | Lapsed due to failure to pay maintenance fee |
Effective date: 20030117 |